Potassium bis(trimethylsilyl)amide → 3-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenol

HRID 1992873Notes

Reaction equation

HRID 1992873 reaction equation
[C:1]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH2:3]([C:2]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([OH:23])[C:8]2[C:7]([CH:1]=1)=[CH:12][C:11]([O:13][CH3:14])=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 685372841-[2-(1-Hexyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone

Product 1

HCID 685373173-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenolYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-[2-(1-hexyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone (80) (0.37 g, 1.21 mmol) in toluene (1.5 mL) was added to a KHMDS solution in toluene (0.5 M, 2.90 mL, 1.45 mmol) at −78° C. under nitrogen. Dry ice bath was removed, the mixture was stirred and allowed to warm up to 0° C., then heated at 80° C. for 1 h. Cooled in an ice bath, the mixture was acidified with 2 N HCl and extracted with ether. The combined ether extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as orange brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (15:1) to give 0.25 g (68%) of 81 as a light brown oil. 1H NMR (400 MHz, CDCl3): δ 0.75 (t, J=7.3 Hz, 3H), 1.10-1.25 (m, 2H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.8 Hz, 2H), 3.92 (s, 3H), 5.15 (s, 1H), 7.05-7.10 (m, 2H), 7.22 (s, 1H), 7.34 (d, J=6.9 Hz, 2H), 7.40-7.50 (m, 1H), 7.50-7.56 (m, 2H), 8.08 (d, J=9.8 Hz, 1H). LCMS (ESI): m/z 307 (M+H)+.

Workup

  1. customDry ice bath was removed
  2. temperatureheated at 80° C. for 1 h
  3. temperatureCooled in an ice bath
  4. extractionextracted with ether
  5. extractionThe combined ether extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customto give the crude product as orange brown oil
  11. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (15:1)

Sources & evidence

ORD record
ord-00233bf146144659aff02f8bc29c73fc
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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